Miss Information: I want to date older women — how do I get them to pay attention to me?

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I want to date older women — how do I get them to pay attention to me?

Stiffler's Mom

Have a question? Email Letters may be edited for length, content, and clarity.

Dear Miss Info,

I've just started with this online-dating thing. I put up a profile on one of the bigger (free) websites, said I was looking for friends and relationships (and, depending on the day, casual sex). And then sat back to see what would happen. I'm a gay dude in my early twenties; people generally consider me to be somewhere between "attractive" and "hot." For the first time in a long while (because of the circles I live in), I was getting all sorts of messages from guys who were interested in me — easily twenty in the first week. Many of them were crap; a few were pretty good. I ended up going on a few dates, and before I fully realized what was happening, I had found myself two guys I was seeing, and sleeping with. One's more or less my physical ideal in a sexual partner; the other's pretty close to the mental ideal. To be fair to them, the handsome one is also rather interesting; the brilliant one is also pretty cute. It's just lopsided.

Ideally, I'd be asking you "which one should I be seeing?" But I don't really think anyone can answer that besides me. My question, instead, is this: at what point, in online dating, am I obligated to turn off my dating profile or set myself as "in a relationship?" When does what I'm doing stop being casual dating and start being me acting like an asshole? Should I just make them aware of each other? My feeling is sort of that once we're officially a couple, this sort of behavior is unacceptable — but what about beforehand? (Am I just struggling for semantics to hold off a difficult decision?)

Online Relationships Put His Ego Under Storm


You get the award for "most thought-out pen name" — I sat here, trying to sound it out, for frigging ages. I sounded like a "Hooked on Phonics" ad circa 1994. So welcome to the column, ORPHEUS! Nice work.

I love this question because it's a variation on the age-old dilemma of "When do I change my Facebook relationship status?" (2006), "Is it too soon to set my Myspace photo to Dan and me totally sucking face?" (2000), or "I'm on Friendster. Does that mean I'm going to die alone?" (always). It's delicate!

The real question here is, are you actively seeking other guys, or at least open to the possibility? If you are, great: keep your account active, and enjoy the flood of new messages. If you're more interested in exploring the possibilities of these two guys, and would rather take a step back from being quite so available, change your account status. There's no shame in either.

The beauty of marking your profile "in a relationship," if you decide to go that route, is that you don't have to be specific. It puts your active internet persona on ice, without asking any bothersome questions like "Oh yeah? With whom?" or "Where do you see yourselves in five years?" or "Will it be a beach wedding? I love beach weddings." And if one of your guys notices the status change and brings it up, just shrug and reply with the truth: "I wanted to stop taking new applicants."

If you decide to keep an active profile, that's fine too. It only becomes "you being a douchebag" when real discussions are being had. As long as you're in the nebulous realm of casual dating, all's fair — but once you start leaning toward one guy over the other, and start heading down the "what are we?" path, then it's no longer appropriate to advertise your availability — or to string the other guy along.

Normally, you'd be under no obligation to tell either guy about the other, but the fact that you're sleeping together makes it murkier, and ultimately touchier. First and foremost, if you have multiple partners, be safe about it. This means condoms every time, and, ideally, some awareness of your partner's sexual track record. Keep yourself and each other safe. (Yeah, yeah, yeah, I'm your eighth-grade gym coach/health teacher. Get over it.) Overall, stay in contact with your gut feelings. As a rule of thumb: if it starts feeling dishonest, then it probably is.

In short, ORPHEUS, I think you're spot-on. You seem to have a good handle on yourself and this situation. Trust your instincts, enjoy getting to know both guys, and you'll do great. You also may want to avoid large groups of women.

Dear Miss Info,

In the past year I've had some new feelings. I'm a thirty-five-year-old single white guy, never married, and for some reason I've found myself looking at online profiles of single women in their fifties & sixties. Now, I don't find all of them attractive, but some I do. If I wanted to pursue some of them, how would I convince them to give me a try, just for something casual? Most are looking for a serious relationship with someone in their own age range. I don't know if I'd want a relationship with them, but more of a fling, just to see what it's like.

Make New Friends, But Keep the Old

Dear Make New Friends,

You are seriously overthinking this. How do you court a sixty-year-old woman? The same way you'd court a twenty-five-year-old one, just with more Matlock. The way to a woman's heart doesn't change much with age. A sixty-year-old has more life experience, so she'll probably be more able to see through bullshit than your standard co-ed. So you may have to up your game. But that just translates to being more direct and honest, which is pretty good advice for any age.

Stop frettting and message a few of the ladies you've had your eye on. Talk to them like you'd talk to a peer — don't let age be a factor. Be thoughtful and pithy, insightful and honest, and you'll be the toast of the bocce court. Maybe most want a LTR with a silver fox, but I guarantee at least a portion of them will be flattered at being approached by a younger guy, excited about that prospect, and totally down for a fling.